19615-48-6Relevant academic research and scientific papers
Lipoxygenase-catalyzed dehydration of furylhydroperoxides
Antonioletti,Bonadies,Monteagudo,Rossi,Scettri
, p. 1919 - 1920 (1992)
3-alkoxycarbonyl-5(1-hydroperoxyalkyl)-furans 1 are changed into the corresponding 5-acyl and 5-formyl derivatives 2 by a lipoxygenase-catalyzed process. The conversion shows to proceed in enantioselective way leading to chiral furylhydroperoxides and furylalcohols. 3-alkoxycarbonyl-5(1-hydroperoxyalkyl)-furans 1 are changed into the corresponding 5-acyl and 5-formyl derivatives 2 by a lipoxygenase-catalyzed process.
Synthesis of (2-Ethoxy-2-oxoethylthio)methyl Derivatives of Furoic Acids and Attempts of Their Intramolecular Cyclizations under the Conditions of the Claisen Reaction
Pevzner, L. M.,Stepanova, N. P.
, p. 166 - 181 (2020)
Abstract: Based on reactions of phosphorylated derivatives of halomethylfuroic acid esters with thioglycolic acid ester in the presence of bases, a method for the synthesis of mono-and bisphosphosphorylated esters of (2-ethoxy-2-oxoethylthio)methyl derivatives of furoic acids, containing an ester group in the position adjacent to the sulfide moiety was developed. Obtained compounds are relatively easily metallized with potassium tert-butylate, but intramolecular cyclization proceeds smoothly only in the case of 5-(diethoxyphosphorylmethyl)-2-(ethoxycarbonylmethylthiomethyl)furan-3-carboxylic acid. The resulting 1,3-dicarbonyl derivative of 7H-thiopyrano[3,4-b]furan is hydrolytically unstable, but its enol O-methyl ether is stabile. Alkaline hydrolysis of the latter compound was studied, and it was shown that it proceeds at the ester as well as at the phosphonate group.
PIPERIDINE DERIVATIVES FOR USE IN THE TREATMENT OF PANCREATIC CANCER
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Page/Page column 63; 64, (2018/03/01)
The present invention relates to novel piperidine derivatives having better cell growth inhibitory activities toward cancer cell cultures and, more particularly, PANC-1 cancer cell cultures than FK866. Accordingly, the present invention relates to compoun
Metal-free syntheses of oxazoles and their analogues based on λ3-iodane-mediated cycloisomerization/functionalization reactions or [2+2+1] cycloaddition type reactions
Saito, Akio
, p. 84 - 98 (2017/04/17)
As a metal-free construction of oxazoles and furans concomitant with the introduction of oxygen functional groups or fluorine atoms into the side chains, we have developed λ3-iodane-mediated cycloisomerization/functionalization reactions of propargyl compounds. In these reactions, aryl- λ3-iodane ArI(X)Y works not only as a donor of heteroatomic functional groups but also as an activator of carbon-carbon triple bonds. Therefore, this methodology is not required any transition metal catalysts, which are frequently used in previous methods. Furthermore, this methodology can be extended to λ3-iodane-mediated [2+2+1] cycloaddition type reactions of alkynes, nitriles and heteroatoms for metal-free formation of oxazoles and imidazoles.
Rapid discovery of potent α-fucosidase inhibitors by in situ screening of a library of (pyrrolidin-2-yl)triazoles
Elias-Rodriguez, Pilar,Moreno-Clavijo, Elena,Carmona, Ana T.,Moreno-Vargas, Antonio J.,Robina, Inmaculada
supporting information, p. 5898 - 5904 (2014/08/05)
The synthesis of a small library of (pyrrolidin-2-yl)triazoles via copper catalysed cycloaddition of an alkynyl iminocyclopentitol and a set of commercial and synthetic azides has been achieved. The in situ screening for the activity towards α-fucosidase of the resulting triazoles has allowed the identification of one of the most potent and selective pyrrolidine derived inhibitors of this enzyme (Ki = 4 nM). This journal is the Partner Organisations 2014.
Synthesis and bioassay of a new class of furanyl-1,3,4-oxadiazole derivatives
El Sadek, Mohamed M.,Hassan, Seham Y.,Abdelwahab, Huda E.,Yacout, Galila A.
, p. 8550 - 8562 (2013/08/23)
Tyrosinase enzyme is a monophenol monoxygenase enzyme, which plays an important role in human as a rate limiting step enzyme for different specific metabolic pathways, as well as its useful application in industry and agriculture. So this study was carried out to test the effect of newly prepared compounds containing 1,3,4-oxadiazoles with different substituted groups on tyrosinase enzyme activity, hoping to use them in the treatment of some diseases arising from tyrosinase activity disorders such as Parkinson's disease, schizophrenia, autism, attention deficit, hyperactivity disorder, and cancer.
PIFA-mediated oxidative cycloisomerization of 2-propargyl-1,3-dicarbonyl compounds: Divergent synthesis of furfuryl alcohols and furfurals
Saito, Akio,Anzai, Toshiyuki,Matsumoto, Asami,Hanzawa, Yuji
experimental part, p. 4658 - 4661 (2011/09/30)
PhI(OCOCF3)2 (PIFA) in the presence of trifluoroacetic acid (TFA) in CH2Cl2 efficiently promotes the oxidative cycloisomerization of 2-propargyl 1,3-dicarbonyl compounds to give 4,5-disubstituted furfuryl alcoho
Reactivity of polyhydroxyalkyl-heterocycles towards Lewis acids
Moreno-Vargas,Fernandez-Bolaos,Fuentes,Robina
, p. 3257 - 3266 (2007/10/03)
We report the reactivity of different polyhydroxyalkyl-heterocycles towards ceric ammonium nitrate (CAN) and ferric chloride. The behaviour of 2-methyl-5-(tetritol-1-yl)-pyrroles and -furans is different towards CAN oxidation. Pyrroles afford 2,5-diformylheterocycles, while furans give access to 1,4-dicarbonyl compounds containing three stereogenic centres. Ferric chloride promotes an intramolecular C-arylation reaction on O-benzylated-polyhydroxyalkyl furans, yielding an isochroman moiety, which is the basic skeleton of a variety of natural products.
Oxidation of polyhydroxyalkyl-heterocycles by cerium (IV). A convenient route to pyrrole-2,5-dicarbaldehydes
Moreno-Vargas, Antonio J.,Robina, Inmaculada,Fernandez-Bolanos, Jose G.,Fuentes, Jose
, p. 9271 - 9274 (2007/10/03)
The synthesis of 3-ethoxycarbonyl-2,5-diformylpyrrole (2) from 3- ethoxycarbonyl-2-methyl-5-D-(arabino-tetritol-l-yl)pyrrole (1) by oxidation with ceric ammonium nitrate is described. When the reaction was applied to related furan derivatives, ethyl (5S,6R,7R)-2-acetyl-5,6,7,8- tetrabenzyloxyoct-2-enoate (8) was obtained as an E/Z mixture.
Phosphorylation of Bromomethyl Derivatives of Cyano-and (2-Alkoxycarbonylethenyl)furans with Trimethyl Phosphite
Pevzner,Ignat'ev,Ionin
, p. 1710 - 1718 (2007/10/03)
Synthetic methods for preparing bromomethyl derivatives of 3-(3-furyl)acrylic acids and also ethoxycarbonylated 3-(2-furyl) and 3-(3-furyl)acrylic acids are developed. Phosphorylation of these compounds with trimethyl phosphite showed that introduction of
